Donald Trump bills himself as a self-made man whose boardroom genius and business acumen make him uniquely qualified to run the country. But excerpts from Trump’s 1995 tax returns, published by The New York Times last weekend, belie the New York billionaire’s self-characterization as one of the nation’s leading real-estate moguls. In fact, by the early 1990s, the Republican nominee’s namesake company was hemorrhaging money and Trump was on the hook for hundreds of millions of dollars. As the Times documents in a new report pulling back the curtain on Trump’s near-financial ruination, the billionaire was careening toward personal bankruptcy following a series of misguided investments and mismanagement of his company in the late 1980s, forcing him to borrow money from his family.

Throughout the election, Trump has continuously referred to himself as the “King of Debt,” but the epithet took on a whole new meaning when the Times published three pages of Donald Trump’s tax returns, received in the mail from an anonymous source, detailing a gargantuan loss of $916 million in 1995—enough to avoid paying income taxes for nearly two decades, according to experts. That near-billion-dollar loss might have been the single biggest net operating loss in the country that year, another expert told the Times in a follow-up story Monday, amounting to almost 2 percent of the the total “net operating losses” reported by all American taxpayers who used the same tax provision as Trump.

The Republican nominee has mostly appeared to take such revelations in stride, boasting at a campaign event in Colorado Monday night that his alleged ability to avoid years of income tax is further evidence of his financial skill. “I was able to use the tax laws in this country and my business acumen to dig out of the real-estate mess—you would call it a depression—when few others were able to do what I did,” he asserted.

That may be so, but it was a mess of Trump’s own making, as further Timesinvestigations make clear. Citing tax documents, interviews, and public records, the paper finds that by 1990 Trump had collected $3.4 billion in debt, of which he was personally liable for $832.5 million. His Atlantic City casinos were bleeding money. Between 1990 and 1991, the Castle casino posted $93.2 million in losses, and in 1991, the Trump Regency hotel and the Trump Plaza casino reported losses of $8.3 million and $29.2 million, respectively. Trump’s ill-advised foray into the airline business resulted in a $34.5 million deficit over a mere six-month period in 1990. He eventually fell $4.1 million behind on his property taxes for a large tract of land in Manhattan and was up against an $18.4 million interest payment at the end of 1990, according to the Times.

While the U.S. economy boomed from 1992 until 2000, Trump fell on such hard times that he reportedly had to tap into his family’s wealth to get out of the hole. In the early 1990s, Trump’s father, Fred, reportedly sent a lawyer to the Castle casino in Atlantic City to buy $3.3 million worth of chips that went uncashed. The Timesreports that Trump took two loans from his siblings, first $10 million and then a subsequent $20 million. (Trump has denied borrowing money from his siblings.) In 1995—the same year he posted a personal $916 million loss—Trump took his Atlantic City casinos public. The decision to offer stock ultimately saved him from financial ruin and as a result, he reportedly pocketed $45 million through 2009 from the venture, even as it continued to lose money.

While it is impossible to know the full extent of Trump’s financial history without seeing more of his tax returns, which he has refused to release, the latest revelations about his past business failures suggest the G.O.P. nominee has reasons to keep his true net worth a secret. As the documents obtained by the Times suggest, Trump may be neither as good a businessman nor as rich as he claims. Any confirmation of that thesis would be a crushing blow, not only to Trump’s presidential campaign, which is built around his self-made mythos, but also to his ego and personal brand. Trump, who quickly lost his composure during the first presidential debate when Hillary Clintonaccused him of having inherited his wealth, has shown time and time again that his greatest insecurities stem from his wallet and that he will go to any lengths to maintain his image. Even in a March 1994 interview with Vanity Fair, Trump tried to spin his story. “As nasty as the press can be, they know that once they’ve cut you down the best story is to build you back up again,” he said, a description that could just as easily describe his sudden political ascendance. “Piece by piece, deal by deal, a beautiful story is starting to emerge about me.”